Issue 12, 2019

Organocatalytic asymmetric synthesis of both cis- and trans-configured pyrano[2,3-b]chromenes via different dehydration pathways

Abstract

The [3 + 3]-cycloaddition reaction of chroman-2-ols with β,γ-unsaturated α-ketoesters via an enamine-catalyzed sequential process is reported. The protocol provides efficient access to polycyclic hemiketal-containing compounds, which could be converted into both enantiomers of cis- and trans-fused pyrano[2,3-b]chromene derivatives with excellent stereoselectivity by different dehydration reaction pathways. The catalytic system could be recycled on a larger scale eight times without significantly affecting the yield and stereoselectivity. The possibilities for further structural diversification are demonstrated by various transformations.

Graphical abstract: Organocatalytic asymmetric synthesis of both cis- and trans-configured pyrano[2,3-b]chromenes via different dehydration pathways

Supplementary files

Article information

Article type
Research Article
Submitted
13 Mar 2019
Accepted
19 Apr 2019
First published
19 Apr 2019

Org. Chem. Front., 2019,6, 1972-1976

Organocatalytic asymmetric synthesis of both cis- and trans-configured pyrano[2,3-b]chromenes via different dehydration pathways

X. Lv, W. Zhao, Y. Chen, S. Wan and Y. Liu, Org. Chem. Front., 2019, 6, 1972 DOI: 10.1039/C9QO00366E

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